(1S,3r,5R)-tert-butyl 3-(tert-butoxycarbonyl)-6-oxa-bicyclo[3.1.0]hexane-3-carboxylate

Base Information

• Chemical Name: (1S,3r,5R)-tert-butyl 3-(tert-butoxycarbonyl)-6-oxa-bicyclo[3.1.0]hexane-3-carboxylate
• CAS No.: 635318-02-4
• Molecular Formula: C15H25NO5
• Molecular Weight: 299.36
• Mol file: 635318-02-4.mol

Synonyms:(1R,5S)-Di-tert-butyl 6-oxabicyclo[3.1.0]hexane-3,3-dicarboxylate;tert-Butyl (1a,3β,5a)-3-(pivaloyloxyamino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate;(1S,3r,5R)-tert-butyl 3-(tert-butoxycarbonyl)-6-oxa-bicyclo[3.1.0]hexane-3-carboxylate;(1R,3s,5S)-tert-Butyl 3-((tert-butoxycarbonyl)aMino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate;6-Oxabicyclo[3.1.0]hexane-3-carboxylic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (1α,3β,5α)-

Chemical Property of (1S,3r,5R)-tert-butyl 3-(tert-butoxycarbonyl)-6-oxa-bicyclo[3.1.0]hexane-3-carboxylate

Chemical Property:

• PSA: 80.65000
• LogP: 2.35720
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(1R,3s,5S)-tert-Butyl3-((tert-butoxycarbonyl)amino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,3r,5R)-tert-butyl 3-(tert-butoxycarbonyl)-6-oxa-bicyclo[3.1.0]hexane-3-carboxylate

There total 13 articles about (1S,3r,5R)-tert-butyl 3-(tert-butoxycarbonyl)-6-oxa-bicyclo[3.1.0]hexane-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate (521964-59-0) → (1α,3β,5α)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-3-carboxylic acid 1,1-dimethylethyl ester (635318-02-4)

Guidance literature:

tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate; With tetra(n-butyl)ammonium hydrogensulfate; magnesium monoperoxyphthalate hexahydrate; In water; ethyl acetate; for 19h;

With sodium sulfite; In water; ethyl acetate; for 0.5h;

Reference yield:

tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate (521964-59-0) → (1α,3β,5α)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-3-carboxylic acid 1,1-dimethylethyl ester (635318-02-4) + (1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane (931396-15-5,635318-02-4)

Guidance literature:

tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate; With sulfuric acid; In ethyl acetate; for 0.0833333h; Large scale;

With magnesium monoperoxyphthalate hydrate; tetra(n-butyl)ammonium hydrogensulfate; In water; ethyl acetate; at 22 ℃; for 22h; Overall yield = 8.70 kg; Large scale;

DOI:10.1021/op060225f

Reference yield:

tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate (521964-59-0) → (1α,3β,5α)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-3-carboxylic acid 1,1-dimethylethyl ester (635318-02-4) + (1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane (931396-15-5,635318-02-4)

Guidance literature:

tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate; With sulfuric acid; In ethyl acetate; for 0.0833333h; Large scale;

With magnesium monoperoxyphthalate hydrate; tetra(n-butyl)ammonium hydrogensulfate; In water; ethyl acetate; at 22 ℃; for 22h; Overall yield = 8.70 kg; Large scale;

DOI:10.1021/op060225f

upstream raw materials:

tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate

methyl t-butyl malonate

3-cyclopentene-1,1-dicarboxylic acid mono(1,1-dimethylethyl) ester

1-(chlorocarbonyl)-1-(tert-butoxycarbonyl)cyclopent-3-ene